Ready to transition from backpack to "Adult" bags

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I think I'm ready to give up my http://ivarpack.com backpack. It has served me very well, but I'm tired of caring something on my back and as ergo friendly as it is, it still kills my back. My typical load is my macbook air in TwelveSouth's Book Book, an iPad, kindle paperwhite, portable hard drive, backup battery, Bose QuietComfort headphones, a couple of books, small journal, pens, bluetooth jawbone and other random stuff. On trips, it is usually the same, but add the kids' iPad and Fire, plus my Nikon D5000. So, my question is, I think I need two bags. One for work and one for trips. Suggestions? I would prefer brown leather and a more rugged look (I'm in academia), but still sleek.

Apparently "adults" prefer dragging little trailers around behind them, unaware of the enlarged blob-print they create in pedestrian flows. And frequently these blob-prints stubbornly engage floorspace perpendicular to the general flow of people, too. So, trading the backpack-that-bangs-into-others-when-jinking for the little wheelie bags that cause different problems is sorta zero-sum for everyone except the backpacker cum trucker. But your back will certainly feel better, I'll bet. Lots of options, too.

Sorry for the snark - neither option is good for others in the vicinity. I use a good shoulder bag from Red Oxx. It's behind me when quickly threading the needle, aside me usually (easy to dip into anytime), and in front when careful navigation is appropriate. And the thing will easily outlast me, too.

This suggestion probably comes to late to help the person who originally asked the question, but I thought I would post anyway for anyone else who might benefit. I found myself asking the same question over a year ago, and for me the answer was Tumi's Everett Essential Tote.

I had my doubts about spending over $300 on a bag, but I have never regretted it even for a second. The bag still looks like new, is capacious, and is very well-designed. It holds all my supplies, has lots of room for books, binders, and my tablet, and side pockets that fit my Lifefactory bottle and umbrella. I use it as my work bag, and I've never run out of room or had trouble finding things in it like I did when I was bringing a backpack to work. If God forbid I ever lost it, I would replace it without thinking twice.

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